


Helping Out a Friend

by ashtonimore



Category: Supernatural
Genre: 5am writing ftw, Destiel - Freeform, M/M, Top!Cas, bottom!Dean, hey i finally wrote something
Language: English
Status: Completed
Published: 2014-12-14
Updated: 2014-12-14
Packaged: 2018-03-01 11:00:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,109
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2770598
Author URL: https://archiveofourown.org/users/ashtonimore/pseuds/ashtonimore
Summary: <blockquote class="userstuff">
              <p>Finally wrote one of my biggest Supernatural headcanons. That Dean lets Castiel do him in 5x03. Enjoy!</p>
            </blockquote>





	Helping Out a Friend

After the whore house disaster, Dean decided they could do for a little R&R back at the house. Castiel was practically crawling out of his skin with discomfort. Let it be known that Dean Winchester’s intentions were pure; he just wanted his friend to get a little action on his last night on Earth. How was Dean possibly supposed to know how badly Castiel was capable of screwing up something so basic? A small chuckle escaped Dean as he recalled the scene at the brothel.

“What is so funny?” Castiel said, a hint of irritation in his voice.

“Dude. You can not go around telling prostitutes that it’s not their fault daddy didn’t love them and expect me not to still be laughing my ass off an hour later.” Dean replied, a shit eating grin plastered on his face. Castiel just gave a small scowl and returned to staring out the window. Jeez. Cas needed to lighten up. Then again, he was still going to die a virgin if things went as expected tomorrow morning. Remembering the whole reason for their little expedition, Dean gave a small frown. With Castiel officially botching prostitution, what was Dean supposed to do now? He tried to put the thought out of his mind, and continued driving.

“I’m…I apologize for what happened Dean,” Castiel suddenly spoke up, turning to face dean with a slightly guilty expression, like a child who’d been caught breaking a rule. “I suppose I am still not used to human interactions.”

                “Well, ya got that right. Man, how long you been on Earth now? How have you still not managed to pick up on the finer points of human communication? When you pop down here, isn’t that like, rule number one? ‘Don’t talk to a prostitute about her daddy issues.’ Don’t they teach you that in angel academy?” Maybe Dean had joked a little too much because the sullen expression on Cas’ face only grew deeper. Couldn’t anybody take a joke?

                Dean gave up on all further attempts at communication and turned his eyes back to the road. They were there anyways. Dean put the Impala into park and clambered out. While walking up to the front door with Castiel close on his heels, a truly absurd thought entered his mind. Oh God. Suddenly, Dean couldn’t stop blushing. He fumbled with the keys to the door, nearly dropping them. He could feel Cas’ eyes boring a hole into his back as he took way too long to open the door. Finally, the universe showed him a little mercy and the door swung wide. Why on Earth would something like _that_ pop into his thoughts? Dean quickly tried his best to shove the thought out of his head.

                Dean began to turn around to talk to Castiel. Regaining his composure was his priority now. He didn’t want Cas to guess what filthy thing had entered his mind. Only, when he turned, there was Castiel, barely an inch away from his face. Dean was pretty sure his entire face was going red at this point. “P…personal space Cas. Come on!” Dean spluttered, watching Castiel do that head tilt thing he did. Castiel made no move to back off and suddenly Dean thought…did he want him to? Oh God Oh God that was dangerous thinking. After the thoughts he had had entering the house, this was not even anywhere near the realm of okay. Bert and Ernie might have been gay, but that didn’t mean Dean needed to be.

                After a series of rapid mental ‘what the fuck’s Dean decided he really just needed to calm down. Castiel was a cool guy. He didn’t know what was going on with Dean. Everything would be fine. Yeah. If he just kept telling himself that maybe it would be true…. After all his inside turmoil, Dean had completely forgotten that he was in kissing distance of Castiel. Oh fuck. Kissing. Castiel. Dean was in deep shit and he knew it. Dean felt his shoulder relax as he resigned himself to the possibility of him and Castiel. John Winchester didn’t raise no queer, but what the hell right? He was dead and a deadbeat anyways.

                Now that Dean had halfway thought about the fact that he might be a lil gay for Cas, he had no idea how to broach the subject of him and Castiel. Would Castiel even be down for something like that? Dean didn’t know if _he_ was. Fuck. Go hard or go home right? He thought maybe a demon had said that to him one time. Taking advice from a demon wasn’t high on his to do list, but it seemed like a solid strategy at the moment. Taking a careful step back, Dean started to talk, trying not to fumble his words and let on how flustered he really was. Dean Winchester: monster hunter, Man Extraordinaire, and scared shitless at the thought of kissing another man. Shit, he was in so deep

                “So uh... Cas,” Dean rambled. “I was thinking earlier. Prostitutes are out right? Well uh…I still can’t have my buddy dying a virgin. What kind of friend would that make me?” Castiel narrowed his eyes, a small redness creeping its way across his cheeks.

                “What are you implying?”

                “Oh uh, well, you know. We could uh……” Dean trailed off, unable to bring the words out of his mouth. Castiel’s eyes widened ever so slightly. Maybe he was going to take the hint and save Dean from his misery.

                “You don’t mean…you and…me?” Castiel let out, speaking cautiously and controlled. Dean felt relief wash down his spine; he wouldn’t have to go through the agony of explaining his intentions to Cas.

                “Well a friend has got to keep his promise right? I can’t have you dying a virgin man.” Dean barely got his words out before Cas closed the distance between them. Dean stumbled backwards, but Castiel crashed his lips against Dean’s and started kissing. It felt like Castiel was trying to channel all of his emotions through his lips. And boy, was Dean receiving. Shocked out of his skull, but not altogether unpleased, Dean started pressing back. He leaned in to the other man and moved his hands on to either side of his face, realizing just how much he had wanted this. Cas’ lips were warm and soft. The kissing was amazing, but it was definitely the scruffiest kiss he’d ever had.

                As Dean moved his body even closer he noticed a growing bugle pressing itself against Dean’s thigh. Two minutes of making out and Cas was already getting hard. Well no one would be criticizing him for lack of enthusiasm, that’s for sure. Not that Dean was complaining. At the feel of Castiel’s cock digging into him, his own groin began to respond with vigor. Before he knew what was happening, they were both rock hard and grinding on each other like a couple of drunken teenagers. Oh God this was hot. Dean silently chastised himself for not putting the moves on Castiel earlier. Who knew letting out your latent homosexual feelings would be so fucking sexy?

                Castiel was the first to break apart their impromptu make out session. Dean resurfaced into reality and gave him a confused look, but all became clear when Castiel started to get down on his knees. Oh shit. Fuck fuck fuck. Was this really happening? Apparently it was because Cas looked up at him and undid Dean’s zipper. He made short work of the clothing barriers between them and had Dean’s fully erect cock pulled out in no time. Castiel only paused to give Dean quite possibly the sexiest look on Earth before putting Dean in his mouth. Dean thought he was going to pass out. Holy shit, he’d had tons of blowjobs before, but this was different. Every slip of Cas’ tongue and every bit of teeth that grazed lightly over  his cock sent waves of pleasure radiating throughout Dean’s body.

                Dean bit his lip, closed his eyes, and tilted his head back. Where the fuck did an angel as old as time learn to give stellar blowjobs? The fuck? Dean moved his hands to back of Castiel head and lightly entwined his fingers through his thick black hair. Castiel continued to go down on Dean with the utmost precision, and Dean was ready to unravel right then and there. He quickly pulled his cock back out of Cas’ mouth and watched a string of spit form between the two. Blushing furiously, he zipped up, ignoring Castiel’s confused expression.

“You’re the one supposed to be getting laid remember?” Dean said as he began to return the favor. Once he got Castiel’s cock out, he was kinda embarrassed. Not only was this the first penis ever to be within 10 inches of his face, but well…Cas was _bigger_ than him. He knew it shouldn’t matter, but oh a man’s ego, how fragile. Regardless, Dean went to work. He hoped that receiving blowjobs wouldn’t be so different from giving them. He had the basic technique down pat anyways. Dean was certainly not prepared for the moans that started coming out of Castiel’s mouth. How was he supposed to concentrate on the job at hand when Cas was letting out the hottest moans of the century?

                After another moment of taking Cas in his mouth Dean slipped back and stoop up. He gave Castiel one last hard kiss and said, “Hey…are you ready for this?” Castiel’s face took on a worried expression, but he nodded and moved closer to Dean. Dean led Castiel down the floor and made him lay down. After removing his many layers, Dean gazed down on Cas’ perfect form. His muscles were enough to make a grown man cry. He removed his own eight layers of clothing (he’d have to rethink wearing so much, if he was ever alone with Cas again) and straddled his legs on either side of Castiel. He spit on his hand and lubed up Castiel’s cock. He could feel it twitch under his hand with anticipation. Or was it longing? Either way Dean began to slowly lower himself onto Cas.

                There weren’t a lot of words to describe Dean’s first time bottoming. He’d been a top all his life so this was definitely something new. The only thing that had ever been in his butt had been one overzealous girlfriend, and Dean had sure put a stop to that pretty quick. No fingers for this man, even though he’d never admit it had felt a little nice. Castiel’s cock entered Dean one inch at a time. Dean went ever so slowly to adjust himself. He found that if he gave himself time, it didn’t hurt that much. He figured this must be just torture to Cas, but hey, he’d live. Forever, if Raphael didn’t get to him first.

                No one prepared Dean for finding his stride. Once he had properly adjusted to having another man’s cock inside of him, he was not at all expecting  it to feel like that. He’d heard once that a man’s G-spot was in his ass, but he hadn’t even considered it might be true. Dean felt spikes of satisfaction ripple through his body as he moved himself up and down on Castiel’s cock. Cas was already breathing heavy and had closed his eyes. Dean leaned forward and took his face in his hands. Cas’ eyes flew open and Dean said, “Hey, look at me. I want to see your face when you come.” Words he’d never thought he’d say to Castiel. Cas looked about twice as turned on by Dean’s words as he had before. Dean increased the speed of his movements and found that Castiel’s hips were rising up to meet him. Three more thrusts upwards and Castiel couldn’t contain himself any longer. Dean felt a thick hot liquid reach into his ass and Dean grabbed his cock. It only took a few quick strokes before he exploded all over Castiel’s chest, painting his pecs in white. Dean basically collapsed on top on Castiel and they laid there, breathing heavily. Finally, Dean rose up a bit and took Castiel out of him; he looked into Cas’ eyes. “So how was that? Not bad for your first time am I right?” Dean spoke with a grin on his face. Castiel nodded tiredly and Dean laughed before leaning in to kiss him. “No matter what happens tomorrow we both better remember this,” Dean said. Castiel wrapped his arm around Dean and they lay there cuddling until they fell asleep. 

**Author's Note:**

> Lemme know if you guys have any feedback you wanna give me! c:


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